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WO2016001129A1 - Compositions insecticides améliorées - Google Patents

Compositions insecticides améliorées Download PDF

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Publication number
WO2016001129A1
WO2016001129A1 PCT/EP2015/064682 EP2015064682W WO2016001129A1 WO 2016001129 A1 WO2016001129 A1 WO 2016001129A1 EP 2015064682 W EP2015064682 W EP 2015064682W WO 2016001129 A1 WO2016001129 A1 WO 2016001129A1
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WO
WIPO (PCT)
Prior art keywords
spp
ammonium
methyl
tetraethylammonium
tetramethylammonium
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PCT/EP2015/064682
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German (de)
English (en)
Inventor
Peter Jeschke
Wolfgang Thielert
Stefan Herrmann
Marita JOHN
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Bayer CropScience AG
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Bayer CropScience AG
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Publication of WO2016001129A1 publication Critical patent/WO2016001129A1/fr
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • the present invention relates to insecticidal compositions comprising the compound of formula (I)
  • At least one effect enhancer preferably selected from ammonium salts, phosphonium salts and penetration promoters.
  • the object of the present invention is therefore to provide an insecticidal composition which contains the compound of the formula (I) and which has an improved action or a broader spectrum of activity than the known compositions.
  • WO 95/017817 describes that the effect of certain agrochemical active ingredients can be increased by the addition of surfactants (detergents) which contain various nitrogen-containing compounds, such as quaternary ammonium salts, betaines and amines.
  • WO 95/017817 is concerned with providing optimized performance enhancers and describes that compositions comprising at least one nitrogen-containing salt and a chelating agent are particularly advantageous.
  • the nitrogen-containing salt is preferably a nitrogen-containing detergent.
  • salts containing nitrogen or phosphorous with longer alkyl and / or aryl substituents are also disclosed in EP-A-0 453 086, EP-A-0 664 081, FR-A-2 600 494, US 4,844,734B, US 5,462,912B , US 5,538,937B, US 20003 / 0224939A, US 2005 / 0009880A and / or US 2005 / 0096386A described.
  • These salts have a permeabilizing effect or increase the solubility of the active ingredient; or they act as detergents.
  • US Pat. No. 2,848,476 B proposes to use salts of sulfonic acids for enhancing the activity (increasing the activity).
  • the effect enhancement can be attributed to the fact that the acids used themselves have a paralyzing effect on insects.
  • inorganic ammonium salts as formulation auxiliaries and enhancers in combination with certain herbicides is also known.
  • WO 92/16108 describes the use of ammonium sulfate as a formulation adjuvant in a granular formulation containing insecticidally active phosphoramidothioates.
  • WO 92/16108 describes that a certain amount of ammonium sulfate is necessary to ensure the chemical stability of granules containing phosphoramidothioates.
  • US 6,645,914 B and EP-A-0 036 106 describe the increase in activity for the herbicides glyphosate and phosphinothricin by adding ammonium sulfate.
  • the effect of the compound of the formula (I) can be increased by the addition of at least one activity enhancer selected from among ammonium and / or phosphonium salts and penetration promoters.
  • composition containing the compound of the formula (I)
  • At least one activity improver selected from penetration promoters (in particular alkanol alkoxylates of the formula (III) as defined below and / or mineral or vegetable oils and their modifications) and ammonium or phosphonium salts of the formula (II)
  • D is nitrogen or phosphorus; preferably D is nitrogen; n is 1, 2, 3 or 4; preferably n stands for 1 or 2;
  • R 8 , R 9 , R 10 and R 11 independently of one another represent hydrogen or in each case optionally substituted C 1 -C 8 -alkyl or mono- or polyunsaturated, optionally substituted C 2 -C 8 -alkenyl, where the substituents are selected from halogen, nitro and cyano can; preferably, R 8, R 9, R 10 and R 11 are independently hydrogen or optionally substituted C i-alkyl, wherein the substituents are selected from halogen, nitro and cyano; particularly preferably R 8, R 9, R 10 and R 11 are independently hydrogen, methyl, ethyl, n-propyl, z o-propyl, n-butyl, z 'o-butyl, eoButyl or tert-butyl; most preferably R 8 , R 9 , R 10 and R 11 are each independently hydrogen, methyl or ethyl;
  • R 12 is an inorganic or organic anion;
  • R 12 is preferably hydrogencarbonate, tetraborate, fluoride, bromide, iodide, chloride, monohydrogenphosphate, dihydrogenphosphate, hydrogensulphate, tartrate, sulphate, nitrate, thiosulphate, thiocyanate, formate, lactate, acetate, propionate, butyrate, pentanoate, citrate or oxalate;
  • R 12 furthermore preferably represents carbonate, pentaborate, sulfite, benzoate, hydrogen oxalate, hydrogen citrate, methyl sulfate or tetrafluoroborate;
  • R 12 particularly preferably represents lactate, sulfate, nitrate, thiosulphate, thiocyanate, citrate, oxalate, formate, monohydrogenphosphate or dihydrogenphosphate;
  • R 12 particularly preferably represents monohydrogenphosphate, dihydrogen
  • ammonium salts of the formula (II) are ammonium sulfate, ammonium lactate, ammonium nitrate, ammonium thiosulphate, ammonium thiocyanate, ammonium citrate, ammonium oxalate, ammonium formate, ammonium hydrogenphosphate,
  • the present invention also provides for the use of the effect enhancers according to the invention, ie the ammonium and / or phosphonium salts according to the invention optionally in combination with the penetration promoters according to the invention, for enhancing the effect (increasing the activity) of the compound of the formula (I).
  • the enhancers may be added to the use solution containing the compound of formula (I) (tank mix / tank mix application) or incorporated into a formulation comprising the compound of formula (I) (formulated product).
  • the invention thus also relates to formulated insecticidal compositions and ready-to-use crop protection agents (for example spray liquors). Finally, the invention also relates to the use of the compositions according to the invention and agents for combating insect pests (plant pests) which occur in agriculture.
  • the compound of the formula (I) can be used in the compositions of the invention in a wide concentration range.
  • the concentration of the compound of the formula (I) in the composition is usually 0.1-50% by weight.
  • ammonium or phosphonium salts of the formula (II) according to the invention can be used in the compositions according to the invention in a wide concentration range.
  • ammonium or phosphonium salts according to the invention are added in the composition in such a concentration that in the ready-to-use plant protection product (in the spray mixture or tank mix / tank mix application) in a concentration of 0.5 to 80 mmol / l, preferably 0.75 to 37.5 mmol / l, particularly preferably 1.5 to 25 mmol / l.
  • the ammonium and / or phosphonium salt concentration in the formulation is chosen such that it is in the aforementioned ranges after dilution of the formulation to the desired drug concentration.
  • the concentration of the salt in the formulation is usually 1-50% by weight.
  • the composition according to the invention contains as an effect enhancer an inventive ammonium and / or phosphonium salt and a penetration promoter according to the invention (in particular alkanol alkoxylates of the formula (III) as defined herein and / or mineral or vegetable oils and their modifications).
  • a penetration promoter according to the invention in particular alkanol alkoxylates of the formula (III) as defined herein and / or mineral or vegetable oils and their modifications).
  • Penetration promoters according to the invention are substances which are usually used to improve the penetration of agrochemical active substances into plants by penetrating from the corresponding application form (in particular aqueous spray mixture) and / or from the spray coating into the cuticle of the plant and thereby increasing the mobility of the material (mobility ) of active ingredients in the cuticle.
  • the method described in the literature can be used to determine this property (Baur et al., 1997, Pesticide Science 51, 131-152).
  • Suitable penetration enhancers are also substances which promote the solubility of the compound of the formula (I) in the spray coating.
  • These include, for example, mineral or vegetable oils (vegetable oils, vegetable oil).
  • Suitable oils are all commonly used in agrochemical means mineral or vegetable - optionally modified - oils in question. Examples include sunflower oil, rapeseed oil, olive oil, castor oil, rapeseed oil, corn oil, cottonseed oil and soybean oil and their esters (preferably methyl or ethyl esters).
  • Preferred oils are rapeseed oil, sunflower oil and their methyl or ethyl esters (e.g., rapeseed oil methyl ester).
  • Suitable penetration enhancers are also alkanol alkoxylates of the formula (III)
  • R is straight-chain or branched C 1 -C 20 -alkyl;
  • R is preferably butyl, where -butyl, n-pentyl, z-pentyl, neopentyl, n-hexyl, iso-hexyl, n-octyl, z o-octyl, 2-ethyl-hexyl, nonyl, where-nonyl, Decyl, n-dodecyl, z o -dodecyl, lauryl, myristyl, z o -tridecyl, trimethyl-nonyl, palmityl, stearyl or eicosyl;
  • R ' is hydrogen, methyl, ethyl, n -propyl, z o -propyl, n -butyl, z o -butyl, tert -butyl, n -pentyl or n -hexyl;
  • AO is an ethylene oxide radical, a propylene oxide radical, a butylene oxide radical or mixtures of ethylene oxide and propylene oxide radicals or butylene oxide radicals; and v is a number from 2 to 30.
  • Suitable penetration promoters are, in particular, alkanol alkoxylates of the formula (IIIa), (IIIb) or (IIIc) R-O - (- EO-) n -R'R-0 - (- EO-) p - (- PO-) q -R'R-0 - (- PO-) r - (- EO-) s -R '
  • PO stands for 3 ; p, q, r, and s each independently represent a number from 1 to 10.
  • Further suitable penetration promoters are in particular alkanol alkoxylates of the formula (III-d)
  • R and R ' have the meanings given above;
  • EO is CH 2 -CH 2 -O-;
  • BO stands for 3 ; p and q, each independently, represent a number from 1 to 10.
  • Further suitable penetration promoters are in particular alkanol alkoxylates of the formula (III-e)
  • EO is CH 2 -CH 2 -O-; each of r and s independently represents a number from 1 to 10.
  • Further suitable penetration promoters are in particular alkanol alkoxylates of the formula (III-f)
  • R ' has the meaning given above; t is a number from 8 to 13; preferably t is a number from 9 to 12; and u is a number from 6 to 17; preferably u is a number from 7 to 9.
  • t is a number from 8 to 13; preferably t is a number from 9 to 12; and u is a number from 6 to 17; preferably u is a number from 7 to 9.
  • An example of an alkanol alkoxylate of the formula (III-c) is a 2-ethylhexyl alkoxylate of the formula (III-c-1)
  • An example of an alkanol alkoxylate of the formula (III-d) is a compound of the formula (III-d-1)
  • alkanol alkoxylates are generally defined by the above formulas. These substances are mixtures of substances of the specified type with different chain lengths. For the indices, therefore, average values are calculated, which can also differ from whole numbers.
  • alkanol alkoxylates of the formulas given are known and are partly available commercially or can be prepared by known methods (compare WO 98/035553, WO00 / 35278 and EP-A 0 681 865).
  • the concentration of penetration promoter can be varied within a wide range in the compositions according to the invention.
  • a formulated crop protection agent In the case of a formulated crop protection agent, it is generally from 1 to 95% by weight, preferably from 1 to 55% by weight, more preferably from 15 to 40% by weight.
  • the concentration In the ready-to-use agents (e.g., spray liquors), the concentration is generally between 0.1 and 10 g / l, preferably between 0.5 and 5 g / l.
  • Pesticide promoter according to the test means that any compound which is suitable for use in the test for penetration of the cuticle according to Baur et al., 1997, Pesticide Science 51, 131 152 acts as a penetration promoter.
  • compositions according to the invention may also contain further components, for example surfactants (nonionic or anionic) or dispersing aids or emulsifiers.
  • Suitable nonionic surfactants or dispersing agents are all substances of this type which can usually be used in agrochemical compositions. Preference is given to polyethylene oxide-polypropylene oxide block copolymers, polyethylene glycol ethers of linear alcohols, reaction products of fatty acids with ethylene oxide and / or propylene oxide, furthermore polyvinyl alcohol, polyvinylpyrrolidone, copolymers of polyvinyl alcohol and polyvinylpyrrolidone and copolymers of (meth) acrylic acid and (meth) acrylic acid esters, furthermore Alkylethoxylates and alkylarylethoxylates, which may optionally be phosphated and optionally neutralized with bases, wherein sorbitol ethoxylates may be mentioned by way of example, as well as polyoxyalkyleneamine derivatives.
  • Suitable anionic surfactants are all substances of this type conventionally usable in agrochemical compositions. Preference is given to alkali metal and alkaline earth metal salts of alkylsulfonic acids or alkylarylsulfonic acids.
  • anionic surfactants or dispersing agents are salts of polystyrenesulfonic acids which are sparingly soluble in vegetable oil, salts of polyvinylsulfonic acids, salts of naphthalenesulfonic acid-formaldehyde condensation products, salts of condensation products of naphthalenesulfonic acid, phenolsulfonic acid and formaldehyde and salts of lignosulfonic acid.
  • Suitable additives which may be present in the formulations according to the invention are emulsifiers, foam-inhibiting agents, preservatives, antioxidants, dyes and inert fillers.
  • Preferred emulsifiers are ethoxylated nonylphenols, reaction products of alkylphenols with ethylene oxide and / or propylene oxide, ethoxylated arylalkylphenols, furthermore ethoxylated and propoxylated arylalkylphenols, and sulfated or phosphated arylalkyl ethoxylates or ethoxypropoxylates, sorbitan derivatives such as polyethylene oxide sorbitan fatty acid esters and sorbitan - fatty acid esters, are exemplified.
  • composition according to the invention may contain, in addition to the compound of formula (I), other active substances, including synergists, and fertilizers.
  • synergists are compounds that increase the effect of the active ingredients without the added synergist itself having to be active.
  • Suitable active ingredients are, for example, the following insecticides, acaricides or nematicides:
  • (Inl) acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC and xylylcarb; or organophosphates, e.g.
  • carbamates e.g. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosul
  • GABA-controlled chloride channel antagonists such as organochlorines, e.g. Chlordane and endosulfan (alpha); or fiproles (phenylpyrazoles), e.g. Ethiprole, Fipronil, Pyrafluprole and Pyriprole.
  • organochlorines e.g. Chlordane and endosulfan (alpha)
  • fiproles phenylpyrazoles
  • Ethiprole e.g. Ethiprole, Fipronil, Pyrafluprole and Pyriprole.
  • nicotinergic acetylcholine receptor agonists such as neonicotinoids, e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, sulfoxaflor, thiacloprid, thiamethoxam; or nicotine.
  • (In6) chloride channel activators such as avermectins / milbemycins, e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
  • juvenile hormone analogs e.g. Hydroprene, kinoprene, methoprene; or fenoxycarb; Pyritexyfen.
  • agents with unknown or nonspecific modes of action such as fumigants, e.g. Methyl bromide and other alkyl halides; or chloropicrin; sulfuryl fluoride; Borax; Tartar emetic.
  • Insect intestinal membrane microbial disruptors such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plant proteins, e.g. CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Abl.
  • Inl2 (Inl2) inhibitors of oxidative phosphorylation, ATP disruptors, such as diafenthiuron; or organotin compounds, e.g. Azocyclotine, cyhexatin, fenbutatin oxide; or propargite; Tetradifon.
  • organotin compounds e.g. Azocyclotine, cyhexatin, fenbutatin oxide; or propargite; Tetradifon.
  • Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap (hydrochloride), thiocylam, and thiosultap (-sodium).
  • Type 0 inhibitors of chitin biosynthesis such as benzoylureas, eg, bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • ecdysone agonists / disruptors such as diacylhydrazines, e.g. Chromafenozide, Halofenozide, Methoxyfenozide and Tebufenozide.
  • (In20) complex III electron transport inhibitors such as hydramethylnone; acequinocyl; Fluacrypyrim.
  • (In21) complex I electron transport inhibitors for example from the group of the METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad; or Rotenone (Derris).
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad; or Rotenone (Derris).
  • (In23) inhibitors of acetyl-CoA carboxylase such as tetronic acid derivatives, e.g. Spirodiclofen and spiromesifen; or tetramic acid derivatives, e.g. Spirotetramat.
  • tetronic acid derivatives e.g. Spirodiclofen and spiromesifen
  • tetramic acid derivatives e.g. Spirotetramat.
  • (In24) complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanide.
  • phosphines e.g. Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanide.
  • ryanodine receptor effectors such as diamides, e.g. Flubendiamide, chlorantraniliprole (Rynaxypyr), cyantraniliprole (Cyazypyr) and 3-bromo-N- ⁇ 2-bromo-4-chloro-6 - [(1-cyclopropylethyl) carbamoyl] phenyl ⁇ -1- (3-chloropyridin-2-yl ) - 1 H -pyrazole-5-carboxamide (known from WO2005 / 077934) or methyl 2- [3,5-dibromo-2 - ( ⁇ [3-bromo-1- (3-chloropyridin-2-yl) -] 1H-pyrazol-5-yl] carbonyl ⁇ amino) benzoyl] -1,2-dimethylhydrazinecarboxylate (known from WO2007 / 043677).
  • diamides e.g. Flubendiamide, chlor
  • Suitable active ingredients are, for example, the following fungicides:
  • (Fl) inhibitors of ergosterol biosynthesis such as aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, dodemorph, Dodemorph Acetate, Epoxiconazole, Etaconazole, Fenarimol, Fenbuconazole, Fenhexamid, Fenpropidin, Fenpropimorph, Fluquinconazole, Flurprimidol, Flusilazole, Flutriafol, Furconazole, Furconazole Cis, Hexaconazole, Imazalil, Imazalil Sulfate, Imibenconazole, Ipconazole, Metconazole, Myclobutanil, Naftifine, Nuarimol, Oxpoconazole, Paclobutrazole, Pefurazoate, Penconazole, Piperaline
  • F2 inhibitors of respiration such as bixafen, boscalid, carboxin, diflumetorim, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, furmecyclox, isopyrazam mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti- more highly enriched racemates 1RS, 4SR, 9SR, isopyrazam (anti-epimeric racemate), isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), isopyrazam (syn-epimeric racemate 1RS , 4SR, 9RS), isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), isopyrazam (syn-epimeric enantiomer 1R, 4S,
  • (F3) inhibitors of respiration at the complex III of the respiratory chain, such as ametoctradine, amisulbrom, azoxystrobin, cyazofamide, dimoxystrobin, enestroburin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin , Pyraoxystrobin, pyribencarb, trifloxystrobin, (2E) -2- (2- ⁇ [6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy ⁇ phenyl) -2- (methoxyimino) -N -methyl-ethanamide, (2E) -2- (methoxyimino) -N-methyl-2- (2- ⁇ [( ⁇ (L (L)
  • (F4) inhibitors of mitosis and cell division such as benomyl, carbendazim, chlorfenazole, diethofencarb, ethaboxam, fluopicolide, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, thiophanate, zoxamide, 5-chloro-7- (4-methylpiperidine-1 - yl) -6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [l, 5-ajpyrimidine and 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4 - (2,4,6-trifluorophenyl) pyridazine.
  • (F5) Compounds with multisite activity, such as Bordeaux mixture, captafol, captan, chlorothalonil, copper preparations such as copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulfate, dichlofluanid, dithianon, dodine, dodine free base, Ferbam, Fluorofolpet, Folpet, guazatine, guazatin acetate , Iminoctadine, iminoctadinal besylate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, zinc metiram, copper oxine, propamidine, propineb, sulfur and sulfur preparations such as calcium polysulfide, thiram, tolylfluanid, zineb and ziram.
  • copper preparations such as copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulfate, dichl
  • (F6) resistance inducers such as acibenzolar-S-methyl, isotianil, probenazole and tiadinil.
  • (F7) inhibitors of amino acid and protein biosynthesis such as andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim and pyrimethanil.
  • (F8) inhibitors of ATP production such as, for example, fentin acetate, fentin chloride, fentin hydroxide and silthiofam.
  • (F9) inhibitors of cell wall synthesis such as benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamide, polyoxins, polyoxorim, validamycin A, and valifenalate.
  • (F10) inhibitors of lipid and membrane synthesis such as biphenyl, chloroneb, dicloran, edifenphos, etridiazole, iodocarb, Iprobenfos, isoprothiolane, propamocarb, propamocarb hydrochloride, prothiocarb, pyrazophos, quintozene, tecnazene, and tolclofos-methyl.
  • (Fl 1) inhibitors of melanin biosynthesis such as carpropamide, diclocymet, fenoxanil, fthalide, pyroquilone and tricyclazole.
  • Inhibitors of nucleic acid synthesis such as benalaxyl, benalaxyl-M (kiralaxyl), bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxolinic acid.
  • Signal transduction inhibitors such as, for example, chlozolinate, fenpiclonil, fludioxonil, iprodione, procymidone, quinoxyfen and vinclozolin.
  • Fl4 decouplers such as binapacryl, dinocap, ferimzone, fluazinam and meptyldinocap.
  • the aforementioned active ingredients can form salts with suitable bases or acids.
  • the active substances mentioned here with their "common name” are known and described, for example, in the Pesticide Handbook ("The Pesticide Manual” 14th Ed., British Crop Protection Council 2006) or searchable on the Internet (eg http://www.alanwood.net/pesticides ).
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including by Plant variety rights protectable or non-protectable plant varieties.
  • Plant parts are to be understood as meaning all aboveground parts and organs of the plants, such as shoots, leaves and flowers, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies and fruits.
  • the plant parts also include crops and vegetative propagating material, such as cuttings.
  • the treatment according to the invention of the plants and plant parts with the composition according to the invention is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, misting, spreading and painting.
  • composition according to the invention is suitable for the treatment of above-ground parts of plants.
  • the present invention therefore also relates in particular to a method of protecting plants from the infestation of plant pests by treating the above-ground parts of plants with the composition according to the invention.
  • the invention also relates to the use of the composition according to the invention for controlling plant pests by applying the composition to conventional or transgenic plants. Furthermore, the invention relates to aboveground plant parts which have been treated with the composition according to the invention for protection against plant pests.
  • plant pests are insects, arachnids, helminths, nematodes and molluscs found in agriculture, horticulture, forests, gardens and recreational facilities.
  • the compositions according to the invention are active against normally sensitive and resistant species as well as against all or individual stages of development. Plant pests include:
  • Pests from the strain Arthropoda, especially from the class of arachnids, e.g. Acarus spp., Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae , Dermatophagoides pteronyssius, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Halotydeus destructor, Hemitarsonemus spp., Hyalomma
  • Apogonia spp. Atomaria spp., Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., Chaetocnema spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Ctenicera spp., Curculio spp., Cryptolestes ferruginus, Cryptorhynchus lapathi, Cylindrocopturus spp., Dermestes spp., Diabrotica spp., Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., Epitrix spp.
  • Tanymecus spp. Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.
  • Dermaptera e.g. Anisolabis maritime, Forficula auricularia, Labidura riparia;
  • Heteroptera e.g. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., Ly
  • Pulvinaria spp. Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella fureifera, Sogatodes spp.
  • Stictocephala festina Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.
  • Hymenoptera e.g. Acromyrmex spp., Athalia spp., Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., Hoplocampa spp., Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis Spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., Wasmannia auropunetata, Xeris spp.
  • Hymenoptera e.g. Acromyrmex spp., Athalia spp., Atta spp., Camponotus spp., Dolichoves
  • Phthorimaea spp. Phthorimaea spp., Phyllocnistis citrella, Phyllonorycter spp., Pieris spp., Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., Pseudaletia unipuncta, Pseudoplusia includens .
  • Phthiraptera eg Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phtirus pubis, Trichodectes spp.
  • Siphonaptera eg Ceratophyllus spp., Ctenocephalides spp., Pulex irritans Tunga penetrans, Xenopsylla cheopis.
  • Thysanoptera e.g. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothris reuteri, Enneothrips flavens, Frankliniella spp., Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
  • Pests from the strain Mollusca, especially from the bivalve class, e.g. Dreissena spp.
  • Gastropoda e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.
  • Plant pests from the strain Nematoda, i. plant parasitic nematodes, in particular Aglenchus spp., Anguina spp., Aphelenchoides spp., Belonolaimus spp., Bursaphelenchus spp., Cacopaurus spp., Criconemella spp., Criconemoides spp., Ditylenchus spp., Dolichodorus spp., Globodera spp.
  • Helicotylenchus spp. Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., Hoplolaimus spp., Longidorus spp., Meloidogyne spp., Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp , Pratylenchus spp., Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., Tylenchul
  • the order of the coccidia for example Eimeria spp., Can be determined from the subregion of the protozoa. fight.
  • One of the advantages of the present invention is that, due to the systemic properties of the composition according to the invention, it is also possible to combat translaminar pests when treating aboveground plant parts.
  • a further advantage consists in the synergistic increase in the insecticidal activity of the composition according to the invention over the individual insecticide, which exceeds the expected effectiveness of the two individually applied active ingredients. This allows optimization of the amount of active ingredients used.
  • the composition of the invention can also be used on transgenic plants, wherein the plants resulting from this seed are capable of expressing a protein directed against pests.
  • the composition of the invention is suitable for the protection of Oberiridisches plant parts of any plant variety, as already mentioned above, which is used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are corn, peanut, canola, rapeseed, poppy, soybeans, cotton, turnip (eg sugar beet and fodder beet), rice, millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables (eg tomatoes , Cabbage).
  • the compositions according to the invention are likewise suitable for the treatment of fruit plants and vegetables as already mentioned above. Special importance is attached to the treatment of maize, soya, cotton, wheat and canola or rapeseed.
  • Transgenic plants usually contain at least one heterologous gene which controls the expression of a polypeptide having in particular insecticidal properties.
  • the heterologous genes in transgenic plants can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for the treatment of transgenic plants containing at least one heterologous gene derived from Bacillus sp. and whose gene product shows activity against corn borer and / or corn rootworm. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • plants and their uppermost parts can be treated.
  • wild-type or plant species and plant varieties obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and parts thereof are treated (conventional plants).
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes.
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants produced by the genetic engineering modification received genetic material which gives these plants special beneficial properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products. Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances.
  • transgenic plants are the important crops such as cereals (wheat, rice), corn, soy, potato, sugar beets, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, and fruit plants (with the fruits apples, pears, citrus fruits and Grapes), with special emphasis on maize, soya, potato, cotton, tobacco and oilseed rape.
  • Traits which are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins formed in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CrylA (a) , CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) in the plants (hereinafter "Bt plants”). Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • trasits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene).
  • herbicidally active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene).
  • the genes which confer the desired properties can also occur in combinations with one another in the transgenic plants.
  • Bt plants are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD ® (for example maize, cotton, soya beans), KnockOut ® (for example maize), StarLink ® (for example maize), Bollgard ® ( cotton), NuCOTN ® (cotton) and NewLeaf ® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties may be mentioned, under the trade names Roundup Ready ® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link ® (tolerance to phosphinotricin, for example oilseed rape), IMI ® (tolerance against imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Roundup Ready ® tolerance to glyphosate, for example maize, cotton, soya bean
  • Liberty Link ® tolerance to phosphinotricin, for example oilseed rape
  • IMI ® tolerance against imidazolinone
  • STS® tolerance to sulfonylureas eg corn
  • Clearfield ® varieties eg corn
  • treatment with the composition according to the invention may also result in superadditive ("synergistic") effects.
  • superadditive for example, reduced application rates and / or extensions of the spectrum of action and / or an increase in the effect of the substances and agents usable in the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering power facilitated harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability of the harvested products, which exceed the actual expected effects.
  • Emulsifier alkylaryl polyglycol ether
  • Rice plants (Oryza sativa, var. Balilla) are treated by spraying with the preparation of active compound in the desired concentration and then populated with larvae of the rice leafhopper ⁇ Nilaparvata lugens).
  • the kill is determined in%. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed.
  • the phytoprotective effect is scored. At 100% effect no damage by feeding is to be seen, with 0% effect the damage at the treated leaves corresponds to the untreated control.
  • the compound of formula (I) in combination with RME (rapeseed oil methyl ester) or / and AMS (ammonium sulfate) showed improved efficacy compared to the single application:
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • emulsifier concentration 1000 ppm until reaching the desired concentration.
  • the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals were killed.
  • Emulsifier alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water When necessary addition of ammonium salts and / or penetration promoters (rapeseed oil methyl ester), these are pipetted in a concentration of 1000 ppm after dilution of the finished preparation solution.
  • Cotton plants (Gossypium hirsutum) are treated by spraying with the preparation of active compound in the desired concentration and then populated with larvae of the green rice bug (Nezara viridula).
  • the phytoprotective effect is scored. At 100% effect no damage by feeding is to be seen, with 0% effect the damage at the treated leaves corresponds to the untreated control.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Compositions contenant le composé de formule (I) et au moins un agent d'amélioration d'effet choisi entre des promoteurs de pénétration et des sels d'ammonium ou de phosphonium de formule (II) dans laquelle D, n, R8, R9, R10, R11 et R12 sont tels que définis dans la description.
PCT/EP2015/064682 2014-07-01 2015-06-29 Compositions insecticides améliorées Ceased WO2016001129A1 (fr)

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EP14175132.1 2014-07-01

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